A cultural gap is widening in English secondary schools: between a twentieth-century ethos of institutional provision and the twenty-first century expectations and digital lifestyles of school students. Perhaps disaffected by traditional teaching methods and the competitive target culture of schools, many students have turned to social networking through the cluster of computer-based applications known as "Web 2.0". Here, they can communicate, share and learn informally using knowledge systems their elders can barely understand. Some of their contemporaries have turned away altogether, rejecting school and contributing to record levels of truancy and exclusion. This paper identifies a set of challenges for school leaders in relation to the growing digital/cultural gap. The government agenda for personalised learning is discussed, alongside strategies which schools might adopt to support this through the use of ICT, and both figure in scenario projections which envision how secondary education could change in the future. The paper concludes by recommending three priorities for school leaders.